US 7,405,228 B2 · Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoprotein sites

Abstract

The present invention provides agents having high antimicrobial activity for preventing and treating infectious diseases. Thus, the present invention provides novel cyano-(substituted)-methylenepiperidinophenyl oxazolidinone derivatives, processes for making the compounds, as well as antimicrobial compositions containing said derivatives as active ingredients and methods of treating bacterial infections with the said derivatives.

A compound of Formula I

or pharmaceutical acceptable salts thereof, wherein
“a” represents a single bond or a double bond;
“b” represents a single bond or a double bond;
wherein
“a” and “b” cannot both be double bonds at the same time;
“A” and “B” are each and independently selected from H, C1-C6 alkyl, CO2Et, or halogen;
when “a” is a double bond, or “a” is a single bond and “A” is not H, CH3, CO2Et, or F
R1 is,
H, C1-C6 alkyl, substituted C1-C6 alkyl, alkenyl, alkynyl, cycloalkyl, substituted cycloalkyl, alkanoyl, substituted alkanoyl, aralkanoyl, substituted aralkanoyl, alkoxycarbonyl, substituted alkoxycarbonyl, thioacyl, substituted thioacyl, aroyl, substituted aroyl, alkylmercapto, arylmercapto, aralkyl, aryl, substituted aryl,
cyano, carboxylic acid, carboxamido, amino, substituted amino, or halogen;
when “a” is a single bond and “A” is H, CH3,CO2Et, or F, then R1 is alkenyl, alkynyl, cycloalkyl, substituted cycloalkyl, alkanoyl, substituted alkanoyl, aralkanoyl, substituted aralkanoyl, alkoxycarbonyl, substituted alkoxycarbonyl, thioacyl, substituted thioacyl, aroyl,
substituted aroyl, alkylmercapto, arylmercapto, aralkyl, aryl, substituted aryl, or carboxamido;
R2 and R3 are the same or different and are hydrogen or halo;
and
R4 is OSO2CH3, amino, mono or di substituted amino, azido, CN, NHCN, N(CN)-allyl, NCO, NHCHO, C1-C6 alkyl amido, substituted C1-C6 alkyl amido, NHCO2CH3, NHCO2Et, NHCO2iPr, NHCO2CH2CH(CH3)2, NHCOCH2OCOC(CH3)3, N(CH3)COCH3, NHCSCH3, NHCSOCH3, NHCSCH2OH, NHCSNHCH2CH2OH, NHCSCH2NH2, NHCONHCH2CH2N(CH3)2, NHCSNH2, NHCSNHCH3, NHSO2CH3, or NHSO2-(3-Me-Ph);
wherein the one or more substituents of substituted C1-C6 alkyl are selected from the group consisting of aryl, hydroxy, methanesulphonyloxy, cyano, halo, amino,and substituted amino groups;
wherein the one or more substituents of substituted cycloalkyl are selected from the group consisting of alkyl, hydroxyl, amino, substituted amino, alkoxycarbonyl, carboximido, cyano and halogen groups;
wherein the one or more substituents of substituted alkanoyl are selected from the group consisting of alkyl, hydroxyl, amino, substituted amino, alkoxycarbonyl, carboxamido, cyano and halogen groups;
wherein the one or more substituents of substituted aralkanoyl are selected from the group consisting of alkyl, hydroxyl, amino, substituted amino, alkoxycarbonyl, carboxamido, cyano and halogen groups;
wherein the one or more substituents of substituted alkoxycarbonyl are selected from the group consisting of alkyl, hydroxyl, amino, substituted amino, alkoxycarbonyl, carboxamido, cyano and halogen groups;
wherein the one or more substituents of substituted thioacyl are selected from the group consisting of alkyl, hydroxyl, amino, substituted amino, alkoxycarbonyl, carboxamido, cyano and halogen groups;
wherein the one or more substituents of substituted aroyl are selected from the group consisting of alkyl, hydroxyl, amino, substituted amino, alkoxycarbonyl, carboxamido, cyano and halogen groups;
wherein the one or more substituents of substituted aryl are selected from the group consisting of alkyl, hydroxyl, amino, substituted amino, alkoxycarbonyl, carboxamido, cyano and halogen groups and
wherein the one or more substituents of substituted amino group are selected from one or more unsubstituted or substituted C1-C3 alkyl groups.

21 more elements

Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoprotein sites

Life of this patent

Antibacterial cyano-(substituted)-methylenepiperidinophenyl oxazolidinones targeting multiple ribonucleoprotein sites

Life of this patent

Abstract

Claims12